EP0364581A1 - Method of sterilizing plant pollen - Google Patents

Method of sterilizing plant pollen Download PDF

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Publication number
EP0364581A1
EP0364581A1 EP19880905465 EP88905465A EP0364581A1 EP 0364581 A1 EP0364581 A1 EP 0364581A1 EP 19880905465 EP19880905465 EP 19880905465 EP 88905465 A EP88905465 A EP 88905465A EP 0364581 A1 EP0364581 A1 EP 0364581A1
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Prior art keywords
plants
treated
methyl
organogenesis
period
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EP19880905465
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German (de)
French (fr)
Inventor
Marat Alexandrovich Fedin
Tatyana Alexandrovna Kuznetsova
Svetlana Alexandrovna Novikova
Vera Nikolaevna Gramenitskaya
Valery Bennovich Berzin
Nina Ivanovna Lukoshina
Ivan Vasilievich Egorov
Nikolai Sigizmundovich Vulfson
Elena Alexeevna Kozmina
Leonid Konstantinovich Voskoboinik
Tatyana Sergeevna Fedorenko
Alexandra Ivanovna Prokopenko
Nadezhda Egorovna Gerasimova
Valentin A. Savchuk
Sergei Ivanovich Paklin
Igor Samuilovich Basin
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Institut Bioorganicheskoi Khimii Imeni Mm Shemyakina Akademii Nauk Ssr
Vsesojuzny Nauchno-Issledovatelsky Inst Selskokhozyaistv Biotekh Vsesojuznoi Ak Selskokhozyaistv Nauk Imeni Vi Lenina
Original Assignee
Institut Bioorganicheskoi Khimii Imeni Mm Shemyakina Akademii Nauk Ssr
Vsesojuzny Nauchno-Issledovatelsky Inst Selskokhozyaistv Biotekh Vsesojuznoi Ak Selskokhozyaistv Nauk Imeni Vi Lenina
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Publication of EP0364581A1 publication Critical patent/EP0364581A1/en
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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing carboxylic groups or thio analogues thereof, directly attached by the carbon atom to a cycloaliphatic ring; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof

Definitions

  • the present invention relates to biology and agriculture, in particular to a method for sterilizing the anthers of plants, which is used in selection and in seed production.
  • gametocides is significantly more economical than that of the system "cytoplasmic pollen sterility", because there is no need for such forms as sterile analogs, analogs for the Fixation of sterility in maternal forms for the restoration of fertility in paternal forms It is practically possible to obtain the seeds of hybrids of the first generation both in the course of the selection research of starting forms and in the organization of their technical production.
  • Gametocides must ensure full pollen sterility in treated plants while maintaining the viability of egg cells and a sufficiently high level Ability to ensure (at least 70% of control desirable) to form the ovary under free pollination. Their phytotoxicity and toxicity values for warm-blooded animals must be minimal.
  • the processes of flower formation and differentiation begin in the fifth period of organogenesis. Towards the end of this period, new formations, sporogenic archespor tissues develop. During this period, stamens, pistils and an inflorescence appear. In the 5th period the differentiation of the cusp from stamens into stamens and pistils appears.
  • the sixth period is characterized by the process of flower formation (micro- and macrosporogenesis). In this period separate mononuclear pollen grains are formed (FMKupermann. Morfofiziologia rasteny. Moskva, izdatelstvo "Vysshaya shkola", 1973, pp. 30-36. Morphophysiology of plants. Moscow, publisher "Vysshaya shkola”, 1973, SS30- 36).
  • Heterocyclic compounds whose main representatives are 2-carboxy-3,4-methane pyrrolidine or 2-methoxy carbonyl-3,4-methane pyrrolidine are used as sterilizing agents.
  • the specified connections are in connection with Diluents and surfactants used.
  • the invention has for its object to develop a method by the choice of sterilizing agents, which can be suitable for sterilizing the anthers of a wide range of cultures with a high degree of sterilization while maintaining the high ability of seeds to form fruit sets with free pollination.
  • the sterilant can be used in conjunction with any known and suitable diluent. It is best to use it in combination with water as a 0.01% aqueous emulsion. Grass plants or sunflower are preferably used as plants which are treated with the specified sterilizing agents.
  • the method according to the invention makes it possible to achieve the male sterility of plants (98-100%) and to obtain a high ability to produce seeds (over 70%).
  • the treatment of plants with the sterilizing agent of the fifth and / or sixth period of organogenesis (according to Kupermann) is repeated.
  • Plants such as Hind and summer wheat, diploid and tetraploid rye, tritale, millet, sunflower etc. are treated with a sterilizing agent, carbonic acid derivatives being used as such.
  • Derivatives of the carboxylic acids can be used in conjunction with any suitable diluents; water is expediently used as the diluent. It is advantageous to use 0.01 to 2% aqueous emulsion of the specified compounds.
  • any suitable surface-active substances can be added to the ready-to-use solutions as desired.
  • any known auxiliaries such as wetting agents, dispersing agents and adhesive agents are usually expediently added to the ready-to-use solutions.
  • the sterilizing agent can be applied to plants using various treatment methods such as liquid atomization and air atomization (aerosols). Plants are treated with the sterilizing agent in the fifth and / or sixth period of organogenesis (according to Kupermann).
  • the dose of the sterilant depends on the nature of the compound, the culture to be treated, the treatment period and natural climate factors. To ensure the high sterilization effect under unfavorable climatic conditions, it is advisable to repeat the treatment of plants in the VI. Period of organogenesis.
  • the total dose of the sterilizing agent is 0.6 to 20 kg / ha.
  • LD50 for phthalic acid dibutyl ester for white mice when introduced once into the stomach is 2838 mg / kg animal weight and for white rats 6669 mg / kg animal weight
  • LD50 for potassium salt of 2-methyl-3-cyclohexene carboxylic acid is 7664 mg / kg animal weight for white rats.
  • the gametocidal activity of the sterilizing agents according to the invention was demonstrated in field trials in various soil climatic zones with sections of 10 m 2 in size in three to four repetitions. Each sterilant has been tested for at least 5 years.
  • Pushing the ears is used to isolate the main ears and other floors in parchment bags.
  • Single insulators are used for wheat and triticals. For rye, one ear of 5 to 7 different plants next to each other is enclosed in a common isolator. With millet, each panicle is isolated separately.
  • the sterility percentage (X) for wheat, rye, tritikale and millet is according to the formula
  • Seeds from untreated control plants determined.
  • the grain count in non-isolated ears of control plants is assumed to be 100% preparation with free pollination.
  • the pollen sterility of plants of the sunflower is assessed according to the pollen fertility and germination capacity, according to the morphological peculiarities of sperm and according to the ability of achenes to start with the pollination of the treated isolated plants with the pollen of the untreated paternal form.
  • the viability of the egg cell is determined after seed formation in treated plants with free pollination of the paternal form.
  • the carboxylic acid derivatives are prepared in a manner known per se.
  • the phthalic acid esters are obtained by esterifying the phthalic anhydride with corresponding alcohols (N.I. Lebedev. Khimia i teohnologia osnovnogo organicheskogo i neftekhimicheskogo sinteza. Moskva, "Khimia", 1981, p. 210).
  • 2-Methyl-3-cyclohexylcarboxylic acid methyl ester is produced by condensing piperylene (the product obtained in petroleum-chemical production) with methyl acrylate (methyl acrylate is widely used in plastics production) in the presence of aluminum chloride (T.Jnukai, Y. Kojima Journal of Organic Chemistry, 32, 869 ,, 1967).
  • the process is carried out analogously to that described in Example 1.
  • the sterilizing agent used is a 2% aqueous emulsion of 2-methyl-3-cyclohexenecarboxylic acid, methyl ester, ammonium salt of 2-methyl-23-cyclohexenecarboxylic acid, phthalic acid dihexyl ester, phthalic acid dibutyl ester, phthalic acid dipropylester, phthalic acid diisobutyl ether.
  • Table 1 The results are shown in Table 1.
  • Plants of the winter wheat variety Polesskaya-70 are treated in the 5th period of organogenesis by atomizing and a 2% aqueous emulsion of diethyl phthalate, diallyphthalate phthalate, diphthalate phthalate, potassium salt of 2-methyl-3-cyclohexene carboxylic acid, ammonium salt of 2-methyl-3-carboxylic acid with the help of a backpack sprayer.
  • the emulsion contains 0.01% by mass of tetrahydrofuran and 0.1% by mass of C 12 -C 14 calcium alkylbenzenesulfonate.
  • the consumption of preparation is 16 kg / ha. Plants are used as a control, treated with the thinner without sterilizing agents.
  • test results are shown in Table 2. The similar results are in the treatment of the winter wheat variety Polesskaya-70 in the VI. Preserved period of organogenesis.
  • Plants of the winter wheat variety Priboi are in the V. and VI. Period of organogenesis (according to Kupermann) treated with a 2% aqueous emulsion of potassium salt of 2-methyl-3-cyclohexenecarboxylic acid, 2-methyl-3-cyclohexenecarboxylic acid methyl ester, phthalic acid dipropyl ester, phthalic acid diisobutyl ester.
  • the emulsion contains 0.01% by weight of dimethyl sulfoxide and 0.1% by weight of C 12 -C 14 calcium alkylbenzenesulfonate.
  • the consumption of the preparation is 12 kg / ha. As Control is served by plants treated with a thinner without sterilizing agents.
  • Plants of winter wheat variety Kharkovskaya 81 are in the V. and VI. Period of organogenesis (according to Kupermann) treated with a 2% aqueous emulsion of sodium salt of 2-methyl-3-cyclohexenecarboxylic acid, phthalic acid dihexyl ester, ammonium salt of 2-methyl-3-cyclohexenocarboxylic acid, phthalic acid dibutyl ester, phthalic acid diallyl ester.
  • the emulsion contains 0.01% by mass of dodezyl sulfate and 0.1% by mass of C 12 -C 14 calcium alkylbenzenesulfonate. The consumption of the preparation is 12 kg / ha.
  • Plants of the summer wheat variety Moskovskaya 35 are grown in the 5th period of organogenesis (according to Kupermann) with a 1% aqueous emulsion of potassium salt of 2-methyl-3-cyclohexene carboxylic acid, 2-methyl-3-cyclohexene carbonate, ethyl ester, phthalic acid dipropylester, phthalic acid dialyl ester, Diisobutyl phthalate, potassium salt of benzoic acid treated.
  • the emulsion contains 0.01% by weight of dimethyl sulfoxide and 0.1% by weight of C 12 -C 14 calcium alkylbenzenesulfonate. The consumption of preparation is 10 kg / ha. Plants are used as a control, treated with a thinner without sterilizing agents.
  • Plants of the summer wheat variety Botanicheskaya 4 are in the 5th period of organogenesis (according to kupermann) with a 1% aqueous emulsion of dibutyl phthalate, diphtyl phthalate, sodium salt of 2-methyl-3-cyclohexenecarboxylic acid, 2-methyl-3-cyclohexenecarboxylic acid methyl- ester treated.
  • the emulsion contains 0.01% by mass of tetrahydrofuran and 0.1% by mass of C 12 -C 14 calcium alkylbenzenesulfonate.
  • the consumption of preparation is 8 kg / ha. Plants are used as a control, treated with a thinner without sterilizing agents
  • Plants of the summer wheat variety Rodina are in the V. and VI. Period of organogenesis (according to Kupermann) with a 1% aqueous emulsion of ammonium salt of the 2-Me treated with ethyl 3-cyclohexene carboxylic acid, phthalic acid dihexyl ester, phthalic acid diisobutyl ester.
  • the emulsion contains 0.01% by mass of dodezysulfate and 0.1% by mass of C 12 -C 14 - calcium alkylbenzenesulfonate.
  • the consumption of the preparation is 6 kg / ha. Plants are used as a control, treated with a thinner without sterilizing agents.
  • Plants Triticals of the PRAG-109 variety are used in the 5th period of organogenesis (according to Kupermann) with a 1% aqueous emulsion of dibutyl phthalate, diethyl phthalate, diphthalate phthalate, diisobutyl phthalate, potassium salt of 2-methyl-3-cyclohexarbonate -3-Cyclohexenkarbon Acidmethylester treated.
  • the emulsion contains 0.01% by weight of dimethyl sulfoxide and 0.1% by weight of C 12 C 14 calcium alkylbenzenesulfonate.
  • the consumption of preparation is 10 kg / ha. Plants are used as a control, treated with a thinner without sterilizing agents.
  • Plants Trical type Amfidiploid 206 are in the 5th period of organogenesis (according to Kupermann) with a 1% aqueous emulsion of phthalic acid dipropyl ester, phthalic acid diisobutyl ester, potassium salt of 2-methyl-3-cyclohexenecarboxylic acid, 2-methyl-3-cyclohexyl carbonic acid, ammonium carbonic acid the 2-methyl-3-cyclohexene carboxylic acid treated.
  • the emulsion contains 0.01% by mass of tetrahydrofuran and 0.1% by mass of C 12 -C 14 calcium alkylbenzenesulfonate. The consumption of the preparation is 6 kg / ha. Plants are used as a control, treated with a thinner without sterilizing agents.
  • test results are shown in Table 9. The similar results are in the treatment of trirical variety Amfiploid 206 in the VI. Preserved period of organogenesis.
  • Plants of tetraploid rye variety Belta are in the 5th period of organogenesis (according to Kupermann) with a 1% aqueous emulsion of potassium salt of 2-methyl-3-cyclohexene carboxylic acid, 2-methyl-3-cyclohexene carboxylic acid methyl ester, phthalic acid dibutyl ester, Treated phthalic acid dihexyl ester, phthalic acid dipropyl ester, phthalic acid diallyl ester, phthalic acid diisobutyl ester, potassium salt of p-hydroxy acid.
  • the emulsion contains 0.01% by weight of dimethyl suloxide and 0.1% by weight of C 12 -C 14 calcium alkylbenzenesulfonate.
  • the consumption of the preparation is 6 kg / ha. Plants treated with a thinner without sterilizing agents serve as a control.
  • test results are shown in Table 10. The similar results are in the treatment of tetraploid rye variety Belta in the VI. Preserved period of organogenesis.
  • Plants of tetraploidal rye of the Ukrainskaya variety are treated in the 5th period of organogenesis (according to Kupermann) with an aqueous emulsion of ammonium salt of 2-methyl-3-cyclohexenecarboxylic acid, diethyl phthalate, potassium salt of benzoic acid, diisocyanate phthalate.
  • the emulsion contains 0.01 mass% dimethylformamide and 0.1 mas se% C12-C14 calcium alkylbenzenesulfonate.
  • the consumption of the preparation is 6 kg / ha. Plants are used as a control, treated with a thinner without sterilizing agents.
  • the test results are shown in Table 11. The similar results are in the treatment of tetraploid rye variety Ukrainskaya in the VI. Preserved period of organogenesis.
  • Plants of diploid rye Chulpan are grown in the 5th period of organogenesis (according to Kupermann) with a 1% aqueous emulsion of potassium salt of 2-methyl-3-cyclohexene carboxylic acid, 2-methyl-3-cyclohexene carboxylic acid methyl ester, potassium salt of Salicylic acid, phthalic acid diallyl ester, phthalic acid diisobutyl ester, phthalic acid dipropyl ester, phthalic acid dihexyl ester, phthalic acid dibutyl ester.
  • the emulsion contains 0.01% by mass of tetrahydrofuran and 0.1% by mass of C12-C14 - calcium alkylbenzenesulfonate. The consumption of preparation is 8 kg / ha. Plants, treated with a thinner without sterilizing agents, serve as an art roll.
  • test results are shown in Table 12. The similar results are in the treatment of diploid rye Chulpan in the VI. Preserved period of organogenesis.
  • Plants of diploid rye variety Kharkovskaya 55 are in the V. and VI. Period of organogenesis (according to Kupermann) with a 1% aqueous emulsion of phthalic acid dibutyl ester, phthalic acid diisobutyl ester, phthalic acid diallyl ester, phthalic acid dihexyl ester, 2-methyl-3-cyclohexene-carboxylic acid methyl ester, sodium salt of 2-methyl-3-cyclohexanoic acid.
  • the emulsion contains 0.01% by weight of dimethylformamide and 0.1% by weight of C 12 C 14 calcium alkylbenzenesulfonate.
  • the consumption of preparation is 6 kp / ha. Plants, treated with a thinner without sterilizing agent, serve as a control.
  • Plants of diploid rye variety Belorusskaya 23 are in the V. and VI. Period of organogenesis (according to Kupermann) treated with a 1% aqueous emulsion of phthalic acid dibutyl ester, potassium salt of 2-methyl-3-cyclohexene carboxylic acid.
  • the emulsion contains 0.01% by mass of dodezyl sulfate and 0.1% by mass of C 12 -C 14 calcium alkylbenzenesulfonate.
  • the consumption of the preparation is 6 kg / ha. Plants are used as a control, treated with a thinner without sterilizing agents.
  • Plants of diploid rye variety Voskhod 2 are in the 5th period of organogenesis (according to Kupermann) with a 1% aqueous emulsion of phthalate, phthal acid diisobutyl ester, potassium salt of 2-methyl-3-cyclohexenecarboxylic acid, ammonium salt of 2-methyl-3-cyclohexenecarboxylic acid, methyl 2-methyl-3-cyclohexenecarboxylate, phthalic acid diallyl ester.
  • the emulsion contains 0.01% by mass of dodezyl sulfate and 0.1% by mass of C 12 -C 14 calcium alkylbenzenesulfonate.
  • the consumption of preparation is 10 kg / ha, plants are used as a control, treated with a thinner without sterilizing agent.
  • test results are shown in Table 15. The similar results are in the treatment of diploid rye Voskhod 2 in the VI. Preserved period of organogenesis.
  • Plants of diploid rye variety Gibrid 1861/79 are in the 5th period of organogenesis (according to Kupermann) with a 1% aqueous emulsion of di-phthalic acid isobutyl ester, potassium salt of 2-methyl-3-cyclohexene carboxylic acid, 2-methyl-3-cyclohexene carboxylic acid methyl ester, Treated ammonium salt of 2-methyl-3-cyclohexenecarboxylic acid, diallyl phthalate, di-phthalate, ammonium salt of p-hydroxybenzoic acid.
  • the emulsion contains 0.01% by weight of dimethyl sulfoxide and 0.1% by weight of C 12 -C 14 calcium alkylbenzenesulfonate. The consumption of the preparation is 6 kg / ha. Plants treated with a thinner without are used as a control Sterilizing agents.
  • test results are shown in Table 16. The similar results are in the treatment of diploid rye variety Gibrid 1861/79 in the VI. Preserved period of organogenesis.
  • Plants of the millet variety Mironovskoe 94 are in the 5th period of organogenesis (according to Kupermann) with a 1% aqueous emulsion of potassium salt of 2-methyl-3-cyclohexenecarboxylic acid, 2-methyl-3-cyclohexenecarboxylic acid methyl ester, phthalic acid dihexyl ester, phthalic acid dibutyl ester, Treated phthalic acid dipropylester, sodium salt of p-hydroxybenzoic acid, diethyl phthalate, diallyl phthalate.
  • the emulsion contains 0.01% by weight of dimethylformamide and 0.1% by weight of C 12 -C 14 calcium alkylbenzenesulfonate.
  • the consumption of preparation is 10 kg / ha. Plants are used as a control, treated with a thinner without sterilizing agents.
  • the test results are shown in Table 17. The similar results are for the treatment of millet variety Mironovskoe 94 in the VI. Preserved period of organogenesis.
  • Plants of the millet variety K-9693 Kormovoe I are in the 5th period of organogenesis (according to Kupermann) with a 1% aqueous emulsion of ammonium salt of 2-methyl-3-cyclonexenecarboxylic acid, phthalic acid dipropyl ester, phthalic acid dibutyl ester, phthalic acid diisobutyl ester, 2-methyl -3-Cyclohexenkarbonklabon Acidmethylester, phthalic acid dihexyl treated.
  • the emulsion contains 0.01% by mass of dodezyl sulfate and 0.1% by mass of C 12 -C 14 calcium alkylbenzenesulfonate.
  • the consumption of preparation is 8 kg / ha. Plants are used as a control, treated with a thinner without sterilizing agents.
  • the test results are shown in Table 18. The similar results are in the treatment of millet variety K-9693 Kormovoe I in VI. Preserved period
  • the sunflower line VK-119 are with a 0.2% aqueous emulsion of phthalic acid dibutyl ester, 0.1% aqueous emulsion of phthalic acid diethyl ester, potassium salt of 2-methyl-3-cyclohexenecarboxylic acid, 1% aqueous emulsion of sodium salt.
  • the emulsion contains 0.01% by weight of dimethylformamide and 0.1% by weight of C 12 -C 14 calcium alkylbenzenesulfonate.

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Abstract

A method of sterilizing plant pollen comprises treating the plants with a sterilizing agent together with a diluent during the fifth and/or the sixth stage of organogenesis. The sterilizing agents used are derivatives of carboxylic acids of the general formula A-COOR, where R is K, Na, NH<4>, alkyl C1-C6, alkyl, ( alpha ), ( beta ), where R<1> is COOH, COOR, H, OH; R<2> is H, OH, or their mixtures.

Description

Technisches GebietTechnical field

Die vorliegende Erfindung bezieht sich auf die Biologie und Landwirtschaft, insbesondere auf ein Verfahren zur Sterilisation der Staubbeutel von Pflanzen, welches in der Selektion und im Samenbau zur Verwendung kommt.The present invention relates to biology and agriculture, in particular to a method for sterilizing the anthers of plants, which is used in selection and in seed production.

Zugrundeliegender Stand der TechnikUnderlying state of the art

Heute wird in der Welt die Aufgabe, die Landwirtschaft zu intensivieren, insbesondere die Ertragsfähigkeit von Getreide-, Futter-, Gemüse- und technischen Kulturen durch breite Verwendung von Hybriden der ersten Generation zu steigern, gelöst, Wegen ihrer Hybridkraft unterscheiden sich die Hybride von den Elternformen in einer höheren Leistung (um 25 bis 30%) und einer besseren Produktqualität. Es besteht ein Verfahren zur Erzeugung von neuen Hybriden, welches auf einem System "zytoplasmatische Pollensterilität - Rosterer der Fertilität" beruht. Diesem Verfahren liegt eine fortwährende (innerhalb von 12 bis 14 Jahren) und komplizierte Selektionsarbeit zugrunde, die das Schaffen von sterilen Analoga, Fixatoren der Sterilität und Restorern der Fertilität umfaßt. Besonders aussichtsreich sind Verfahren, die auf der Sterilisation der Staubbeutel von Pflanzen mit chemischen Sterilisationsmitteln (Gametoziden basieren. Die Verwendung von Gametoziden ist bedeutend wirtschaftlicher als die des Systems "zytoplasmatische Pollensterilität", weil die Notwendigkeit entfällt, solche Formen wie steriles Analogon, Analogon für die Fixierung der Sterilität bei mütterlichen Formen für die Restauration der Fertilität bei väterlichen Formen zu erzeugen. Man kann praktisch die Samen von Hybriden der ersten Generation sowohl im Laufe der Selektionsforschung von Ausgangsformen als auch bei der Organisation ihrer technischen Herstellung gewinnen.Today, the task of intensifying agriculture, in particular increasing the productivity of cereals, feed, vegetables and technical crops through wide use of first-generation hybrids, is solved in the world. Because of their hybrid power, the hybrids differ from those Parent forms in a higher performance (by 25 to 30%) and a better product quality. There is a process for the production of new hybrids, which is based on a system "cytoplasmic pollen sterility - roster of fertility". This process is based on an ongoing (within 12 to 14 years) and complicated selection work, which includes the creation of sterile analogs, fixators of sterility and restorers of fertility. Particularly promising are methods which are based on the sterilization of the anthers of plants with chemical sterilizing agents (gametocides. The use of gametocides is significantly more economical than that of the system "cytoplasmic pollen sterility", because there is no need for such forms as sterile analogs, analogs for the Fixation of sterility in maternal forms for the restoration of fertility in paternal forms It is practically possible to obtain the seeds of hybrids of the first generation both in the course of the selection research of starting forms and in the organization of their technical production.

Zur Zeit sind etwa 200 Verbindungen gefunden, welche eine gametozide Aktivität besitzen und ihrer chemischen Struktur nach zu verschiedenen Klassen von chemischen Verbindungen gehören. Gametozide müssen die volle Pollensterilität bei behandelten Pflanzen unter Erhaltung der Lebensfähigkeit von Eizellen bewirken und eine ausreichend hohe Fähigkeit (wünschenswert mindenstens 70% der Kontrolle), den Fruchtknoten unter freier Bestäubung zu bilden, sicherstellen. Die Werte ihrer Phytotoxizitat und Toxizität für Warmblüter müssen minimal sein.Around 200 compounds are currently found which have gametocidal activity and whose chemical structure belongs to different classes of chemical compounds. Gametocides must ensure full pollen sterility in treated plants while maintaining the viability of egg cells and a sufficiently high level Ability to ensure (at least 70% of control desirable) to form the ovary under free pollination. Their phytotoxicity and toxicity values for warm-blooded animals must be minimal.

Bekannt sind Verfahren zur Sterilisation der Staubbeutel von GetreideKulturen (L.Dzh. Nikell. Regulatory rosta rasteny. Primenenie v selskom khozyaistve. Moskva, izdatelstvo "Kolos", 1984, S. 28-31; SU, A, 906457. L.J. NiKell. Wachstumsregulatoren von Pflanzen. Anwendung in der Landwirtschaft. Moskau, Verlag "Kolos", 1984, S. 28-31), welche in der Behandlung von Pflanzen mit Sterilisationsmitteln wie 2-Chloräthylphosphonsäure (Ethrel), Maleinsäurehydrazid, Di-(polyfluoralkyl)-phosphorsäuren und ihre Salze u.a. bestehen. Die Behandlung der Pflanzen mit einheimischen Sterilisationsmitteln erfolgt in der V. und/oder VI. Periode der Organogenese (nach F. M. Kupermann).Methods are known for sterilizing the anthers of cereal cultures (L.Dzh. Nikell. Regulatory rosta rasteny. Primenenie v selskom khozyaistve. Moskva, izdatelstvo "Kolos", 1984, pp. 28-31; SU, A, 906457. LJ NiKell. Growth regulators of plants, application in agriculture. Moscow, publisher "Kolos", 1984, pp. 28-31), which are used in the treatment of plants with sterilizing agents such as 2-chloroethylphosphonic acid (Ethrel), maleic hydrazide, di (polyfluoroalkyl) phosphoric acids and their salts etc. consist. The plants are treated with domestic sterilization agents in the V. and / or VI. Period of organogenesis (after F. M. Kupermann).

In der V. Periode der Organogenese setzen die Prozesse der Bildung und der Differenzierung von Blüten ein. Gegen Ende dieser Periode entstehen Neubildungen, sporogene Archesporgewebe. Während dieser Periode kommt es zur Anlegung von Staubblättern, Stempel und Blütenhülle. In der V. Periode tritt die Differenzierung des Höckers von Staubblättern in Staubfaden und Stempel in Erscheinung. Die VI.Periode ist durch Ablauf der Prozesse der Blütenbildung (Mikro- und Makrosporogenese) gekennzeichnet. In dieser Periode werden gesonderte einkernige Pollenkörner gebildet (F.M.Kupermann. Morfofiziologia rasteny. Moskva, izdatelstvo "Vysshaya shkola", 1973, S. S, 30-36. Morphophysiologie von Pflanzen. Moskau, Verlag "Vysshaya shkola", 1973, S.S.30-36).The processes of flower formation and differentiation begin in the fifth period of organogenesis. Towards the end of this period, new formations, sporogenic archespor tissues develop. During this period, stamens, pistils and an inflorescence appear. In the 5th period the differentiation of the cusp from stamens into stamens and pistils appears. The sixth period is characterized by the process of flower formation (micro- and macrosporogenesis). In this period separate mononuclear pollen grains are formed (FMKupermann. Morfofiziologia rasteny. Moskva, izdatelstvo "Vysshaya shkola", 1973, pp. 30-36. Morphophysiology of plants. Moscow, publisher "Vysshaya shkola", 1973, SS30- 36).

Bekannt ist weiter ein Verfahren zur Sterilisation der Staubbeutel von Graspflanzen (GB, A, 1567153), das darin besteht, daß man die Behandlung von Graspflanzen mit einem Sterilisationsmittel in der Periode durch führt, die zwischen Auftreten des zweiten Stengelglieds und Ährenschieben liegt. Als Sterilisationsmittel verwendet man heterozyklische Verbindungen, deren Hauptvertreter 2-Karboxy-3,4-me- thanpyrrolidin oder 2-Methoxykarbonyl-3,4-methanpyrrolidin sind. Die angegebenen Verbindungen werden in Verbindung mit Verdünnungsmitteln und oberflächenaktiven Stoffen eingesetzt.Also known is a method for the sterilization of the anthers of grass plants (GB, A, 1567153), which consists in that the treatment of grass plants with a sterilizing agent is carried out in the period between the occurrence of the second stem member and the pushing of ears. Heterocyclic compounds whose main representatives are 2-carboxy-3,4-methane pyrrolidine or 2-methoxy carbonyl-3,4-methane pyrrolidine are used as sterilizing agents. The specified connections are in connection with Diluents and surfactants used.

Offenbarung der ErfindungDisclosure of the invention

Die Erfindung liegt die Aufgabe zugrunde, durch die Wahl von Sterilisationsmitteln ein Verfahren zu entwickeln, welches zur Sterilisation der Staubbeutel eines breiten Spektrums von Kulturen mit hohem Sterilisationsgrad unter Erhaltung der hohen Fühigkeit von Samen, Fruchtansätze bei freier Bestäubung zu bilden, geeignet werden kann.The invention has for its object to develop a method by the choice of sterilizing agents, which can be suitable for sterilizing the anthers of a wide range of cultures with a high degree of sterilization while maintaining the high ability of seeds to form fruit sets with free pollination.

Diese Aufgabe wird dadurch gelöst, daß im vorgeschlagenen Verfahren zur Sterilisation der Staubbeutel von Pflanzen durch ihre Behandlung mit einem Sterilisationsmittel in Verbindung mit einem Verdünner in der fünften und/oder sechsten Periode der Organogenese erfindungsgemäß als Sterilisationsmittel Karbonsäurederivate der allgemeinen Formel A-COOR, dienen, worin R für K, Na, NH4, Alkyl mit 1 bis 6 Kohlenstoffatomen, Allyl steht,

Figure imgb0001
bedeutet, worin R1 = COOH, COOR, H, OH ist;

  • R2 für H, OH steht, oder Gemische derselben verwendet..
This object is achieved in that, according to the invention, carboxylic acid derivatives of the general formula A-COOR serve as sterilizing agents in the proposed method for sterilizing the anthers of plants by treating them with a sterilizing agent in conjunction with a thinner in the fifth and / or sixth period of organogenesis, where R is K, Na, NH 4 , alkyl having 1 to 6 carbon atoms, allyl,
Figure imgb0001
 means wherein R 1 = COOH, COOR, H, OH;
  • R 2 represents H, OH, or mixtures thereof ..

Das Sterilisationsmittel kann in Verbindung mit einem beliebigen bekannten und dazu geeigneten Verdünner verwendet werden. Es ist zweckmäßigerweise in Kombination mit Wasser als 0,01%ige wäßrige Emulsion zu benutzen. Als Pflanzen, die mit angegebenen Sterilisationsmittel behandelt werden, dienen bevorzugt Graspflanzen oder Sonnenblume.The sterilant can be used in conjunction with any known and suitable diluent. It is best to use it in combination with water as a 0.01% aqueous emulsion. Grass plants or sunflower are preferably used as plants which are treated with the specified sterilizing agents.

Das erf indungsgemäße Verfahren ermöglicht, die männliche Sterilität von Pflanzen (98-100%) zu erzielen und eine hohe Fähigkeit zur Samenbildung (über 70%) zu erhalten. Zwecks Erzielung des hohen Sterilisationsgrades von Staubbeuteln unter ungünstigen Klimabedingungen wird die Behandlung von Pflanzen mit dem Sterilisationsmittel der fünften und/oder sechsen Periode der Organogenese (nach Kupermann) wiederholt.The method according to the invention makes it possible to achieve the male sterility of plants (98-100%) and to obtain a high ability to produce seeds (over 70%). In order to achieve the high degree of sterilization of anthers under unfavorable climatic conditions, the treatment of plants with the sterilizing agent of the fifth and / or sixth period of organogenesis (according to Kupermann) is repeated.

Beste Ausführungsform der ErfindungBest embodiment of the invention

Das erfindungsgemäße Verfahren wird wie folgt durchgeführt.The method according to the invention is carried out as follows guided.

Pflanzen wie z.B. hinter- und Sommerweizen, diploider und tetraploider Roggen, Tritikale, Hirse, Sonnenblume u.a. werden mit einem Sterilisationsmittel behandelt, wobei als solches Karbonsäurederivate verwendet werden.Plants such as Hind and summer wheat, diploid and tetraploid rye, tritale, millet, sunflower etc. are treated with a sterilizing agent, carbonic acid derivatives being used as such.

Derivate der Karbonsäuren können in Verbindung mit beliebigen geeigneten Verdünnern verwendet werden, als Verdünner ist Wasser zweckmäßigerweise zu benutzen. Dabei ist 0,01- bis 2%ige wäßrige Emulsion der angegebenen Verbindungen vorteilhaft zu verwenden.Derivatives of the carboxylic acids can be used in conjunction with any suitable diluents; water is expediently used as the diluent. It is advantageous to use 0.01 to 2% aqueous emulsion of the specified compounds.

Man kann den gebrauchsfertigen Lösungen beliebige geeignete oberflächenaktive Stoffe wunschgemäß zusetzen. Beim Aufbringen auf die Pflanzen sind gewöhnlich den gebrauchsfertigen Lösungen beliebige bekannte Hilfsmittel wie Netzmittel, Dispergiermittel und Adhäsionsmittel zweckmäßigerweise hinzuzufügen.Any suitable surface-active substances can be added to the ready-to-use solutions as desired. When applied to the plants, any known auxiliaries such as wetting agents, dispersing agents and adhesive agents are usually expediently added to the ready-to-use solutions.

Das Sterilisationsmittel läßt sich auf Pflanzen nach verschiedenen Behandlungsverfahren wie Flüssigkeitszerstäubung und Luftzerstäubung (Aerosole) aufbringen. Die Behandlung von Pflanzen mit dem Sterilisationsmittel erfolgt in der fünften und/oder sechsten Periode der Organogenese (nach Kupermann). Die Dosis des Sterilisationsmittels hängt von der Natur der Verbindung, von zu behandelnder Kultur, Behandlungsperiode und natürlichen Klimafaktoren ab. Um den hohen Sterilisationseffekt unter ungünstigen Klimabedingungen sicherzustellen, ist es zweckmäßig, die wiederholte Behandlung von Pflanzen in der VI. Periode der Organogenese durchzuführen. Die Gesamtdosis des Sterilisationsmittels beträgt 0,6 bis 20 kg/ha.The sterilizing agent can be applied to plants using various treatment methods such as liquid atomization and air atomization (aerosols). Plants are treated with the sterilizing agent in the fifth and / or sixth period of organogenesis (according to Kupermann). The dose of the sterilant depends on the nature of the compound, the culture to be treated, the treatment period and natural climate factors. To ensure the high sterilization effect under unfavorable climatic conditions, it is advisable to repeat the treatment of plants in the VI. Period of organogenesis. The total dose of the sterilizing agent is 0.6 to 20 kg / ha.

Alle erfindungsgemäßen Karbonsäurederivate, die als Sterilisationsmittel zur Verwendung kommen, waren auf die akute Toxizität im Tierversuch geprüft. Die Prüfergebnisse haben ergeben, daß die angegebenen Verbindungen von schwacher oder mittlerer Toxizität sind. So beträgt, beispielsweise, LD50 bei Phthalsäuredibutylester für weiße Mäuse bei der einmaligen Einführung in den Magen 2838 mg/kg Tiergewicht und für weiße Ratten 6669 mg/kg Tiergewicht, LD50 bei Kaliumsalz der 2-Methyl-3-zyklohexenkarbonsäure- beträgt für weiße Ratten 7664 mg/kg Tiergewicht.All carboxylic acid derivatives according to the invention, which are used as sterilizing agents, were tested for acute toxicity in animal experiments. The test results have shown that the compounds indicated are of low or medium toxicity. For example, LD50 for phthalic acid dibutyl ester for white mice when introduced once into the stomach is 2838 mg / kg animal weight and for white rats 6669 mg / kg animal weight, LD50 for potassium salt of 2-methyl-3-cyclohexene carboxylic acid is 7664 mg / kg animal weight for white rats.

Die gametozide Aktivität der erfindungsgemäßen Sterilisationsmittel war in Feldversuch in verschiedenen bodenklimatischen Zonen mit Teilstücken von 10 m2 Größe in drei-- bis viermaliger Wiederholung nachgewiesen. Jedes Sterilisationsmittel wurde mindestens 5 Jahre lang geprüft.The gametocidal activity of the sterilizing agents according to the invention was demonstrated in field trials in various soil climatic zones with sections of 10 m 2 in size in three to four repetitions. Each sterilant has been tested for at least 5 years.

Die Entwicklung der Perioden der Organogenese wird zytologisch überwacht. Die Behandlung von Pflanzen mit dem Sterilisationsmittel erfolgt am Anfang der fünften Periode der Organogenese nach Kupermann.The development of the periods of organogenesis is monitored cytologically. Plants are treated with the sterilizing agent at the beginning of the fifth period of Kupermann organogenesis.

Mit dem Ahrenschieben verwirklicht man die Isolierung von Hauptähren und anderen Stockwerken in Pergamentbeuteln. Bei Weizen und Tritikale werden Einzelisolatoren verwendet. Bei Roggen schließt man je 1 Ähre von 5 bis 7 verschiedenen nebeneinander befindlichen Pflanzen in einen gemeinsamen Isolator ein. Bei Hirse wird jede Rispe getrennt isoliert. Der Sterilitätsprozentsatz (X) für Weizen, Roggen, Tritikale und Hirse wird nach der Formel

Figure imgb0002
Pushing the ears is used to isolate the main ears and other floors in parchment bags. Single insulators are used for wheat and triticals. For rye, one ear of 5 to 7 different plants next to each other is enclosed in a common isolator. With millet, each panicle is isolated separately. The sterility percentage (X) for wheat, rye, tritikale and millet is according to the formula
Figure imgb0002

Samen von unbehandelten Kontrollpflanzen ermittelt.Seeds from untreated control plants determined.

Die Kornzahl in nicht isolierten Ähren von Kontrollpflanzen wird bedingt für 100% Ansetzen bei freier Bestäubung angenommen.The grain count in non-isolated ears of control plants is assumed to be 100% preparation with free pollination.

Um zuverlässige Angaben zu erhalten, verwendet man 20 bis 25 Isolatoren jeder Wiederholung für Weizen und Tritikale, 10 bis 15 Isolatoren jeder Wiederholung für Roggen und Hirse.In order to obtain reliable information, 20 to 25 isolators of each repetition are used for wheat and tritale, 10 to 15 isolators of each repetition for rye and millet.

Zur Kontrolle der chemischen Sterilisation des Sonnenblumenpollens werden für jede Verbindung 45 behandelte Pflanzen jeder Wiederholung benutzt, wobei 15 Pflanzen zwecks Selbsbestäubung isoliert werden, Blutenkörbchen von 15 anderen Pflanzen mit einem Pollengemisch, gesammelt von 20 bis 25 behandelten isolierten Körbchen, bestäubt werden, und 15 Pflanzen für freie Bestäubung gelassen werden, damit das Ansetzen von Achänen mit dem Pollen der Vaterform kontrolliert werden kann.To control the chemical sterilization of sunflower pollen, 45 treated plants of each repetition are used for each compound, 15 plants being isolated for self-pollination, 15 baskets of 15 other plants with a pollen mixture collected from 20 to 25 treated isolated cups, and 15 plants be left for free pollination so the setting of achenes with the pollen of the father form can be controlled.

Man beurteilt die Pollensterilität von Pflanzen der Sonnenblume nach der Pollenfertilität und -keimfahigkeit, nach den morphologischen Besonderheiten von Spermien und nach der Fähigkeit von Achänen zum Ansetzen bei der Bestäubung der behandelten isolierten Pflanzen mit dem Pollen der unbehandelten väterlischen Form. Die Läbensfähigkeit der Eizelle wird nach der Samenbildung bei behandelten Pflanzen bei freier Bestäubung der väterlichen Form bestimmt.The pollen sterility of plants of the sunflower is assessed according to the pollen fertility and germination capacity, according to the morphological peculiarities of sperm and according to the ability of achenes to start with the pollination of the treated isolated plants with the pollen of the untreated paternal form. The viability of the egg cell is determined after seed formation in treated plants with free pollination of the paternal form.

Es ist wünschenswert, die Behandlung von Pflanzen bei heiterem windstillem Wetter durchzuführen.It is desirable to treat plants in clear windless weather.

Alle Verbindungen dringen in Pflanzengewebe innerhalb von 4 Stunden nach der Behandlung vollständig ein. Bei den atmosphärischen Niederschlägen im Verlaufe dieser vierstündigen Zeitspanne ist es notwendig, die Pflanzen in der VI. Periode der Organogenese wiederholt zu behandeln. Die Karbonsäurederivate stellt man in an sich bekannter Weise her .All compounds fully penetrate plant tissue within 4 hours of treatment. With the atmospheric precipitation during this four-hour period, it is necessary to plant the plants in the VI. Treat period of organogenesis repeatedly. The carboxylic acid derivatives are prepared in a manner known per se.

Die Phthalsäureester gewinnt man durch Veresterung des Phthalsäureanhydrids mit entsprechenden Alkoholen (N.I. Lebedev. Khimia i teohnologia osnovnogo organicheskogo i neftekhimicheskogo sinteza. Moskva, "Khimia", 1981, S. 210). Man stellt 2-Methyl-3-zyklohexylkarbonsäuremethyl- ester durch Kondensation von Piperylen (das bei der erd- ölchemischen Produktion anfallende Produkt) mit Methylakrylat (Methylakrylat wird bei der Plastherstellung breit verwendet) in Gegenwart von Aluminiumchlorid her (T.Jnukai, Y. Kojima Journal of organic Chemistry, 32, 869,, 1967). Durch Verseifung des oben genannten Esters mit Kalium- Natrium- oder Ammoniumhydroxid stellt man entsprechende Salze der 2-Methyl-3-zyklohexylkarbonsäure her. Das Kalium-, Natrium- bzw. Ammoniumsalz der Benzoe-, p-Hydroxybenzoe- bzw. Salizylsäure erhält man durch ihre Neutralisation mit entsprechenden Hydroxiden.The phthalic acid esters are obtained by esterifying the phthalic anhydride with corresponding alcohols (N.I. Lebedev. Khimia i teohnologia osnovnogo organicheskogo i neftekhimicheskogo sinteza. Moskva, "Khimia", 1981, p. 210). 2-Methyl-3-cyclohexylcarboxylic acid methyl ester is produced by condensing piperylene (the product obtained in petroleum-chemical production) with methyl acrylate (methyl acrylate is widely used in plastics production) in the presence of aluminum chloride (T.Jnukai, Y. Kojima Journal of Organic Chemistry, 32, 869 ,, 1967). Saponification of the above-mentioned ester with potassium, sodium or ammonium hydroxide produces corresponding salts of 2-methyl-3-cyclohexylcarboxylic acid. The potassium, sodium or ammonium salt of benzoic, p-hydroxybenzoic or salicylic acid is obtained by neutralizing it with appropriate hydroxides.

Zum besseren Verstehen der vorliegenden Erfindung werden folgende konkrete Ausführungsbeispiele angeführt.The following specific exemplary embodiments are given for a better understanding of the present invention.

Beispiel 1example 1

Pflanzen des Winterweizens Sorte Mironovskaya 808 werden in der V. Periode der Organogenese durch Zerstäubung einer 2%igen wäßrigen Emulsion des Kaliumsalzes von 2-Methyl-3-zyklohexenkarbonsäure mit Hilfe einer Rückenspritze behandelt. Als Emulgiermittel setzt man 0,1 Masse% C12--C14 - Kalziumalkylbenzolsulfonat zu. Als Adjuvans führt man in die Emulsion 0,01 Masse% Dimethylformamid ein. Der Verbrauch an Präparat beträgt 20 kg/ha. Als Kontrolle dienen Pflanzen, behandelt mit einem Verdünner ohne Sterilisationsmittel. Die Ergebnisse sind in der Tabelle 1 angegeben. Die ähnlichen Ergebnisse sind bei der Behandlung des Winterweizens Sorte Mironovskaya 808 in der VI. Periode der Organogenese erhalten.Winter wheat plants of the Mironovskaya 808 variety are treated in the 5th period of organogenesis by spraying a 2% aqueous emulsion of the potassium salt of 2-methyl-3-cyclohexene carboxylic acid with a sprayer. 0.1% by mass of C 12 -C 14 calcium alkylbenzenesulfonate is added as emulsifier. As an adjuvant, 0.01% by mass of dimethylformamide is introduced into the emulsion. The consumption of preparation is 20 kg / ha. Plants are used as a control, treated with a thinner without sterilizing agents. The results are shown in Table 1. The similar results are in the treatment of winter wheat variety Mironovskaya 808 in VI. Preserved period of organogenesis.

Beispiele 2-8Examples 2-8

Der Prozeß wird analog zu dem in Beispiel 1 beschriebenen durchgeführt. Als Sterilisationsmittel verwendet man eine 2%ige wäßrige Emulsion von 2-Methyl-3-zyklohexenkarbon- säuremethylester, Ammoniumsalz der 2-Methyl-23-zyklohexen- karbonsäure, Phthalsäuredihexylester, Phthalsäuredibutylester, Phthalsäuredipropylester, Phthalsäurediisobutylester, Phthalsäurediäthylester. Die Ergebnisse sind in der Tabelle 1 angeführt.The process is carried out analogously to that described in Example 1. The sterilizing agent used is a 2% aqueous emulsion of 2-methyl-3-cyclohexenecarboxylic acid, methyl ester, ammonium salt of 2-methyl-23-cyclohexenecarboxylic acid, phthalic acid dihexyl ester, phthalic acid dibutyl ester, phthalic acid dipropylester, phthalic acid diisobutyl ether. The results are shown in Table 1.

Die ähnlichen Ergebnisse sind bei der Behandlung des Weizens Sorte Mironovskaya 808 in der VI. Periode der Organogenese erhalten.

Figure imgb0003
The similar results are in the treatment of wheat variety Mironovskaya 808 in VI. Preserved period of organogenesis.
Figure imgb0003

Beispiele 9-13Examples 9-13

Pflanzen des Winterweizens Sorte Polesskaya-70 behandelt man in der V. Periode der Organogenese durch Zerstäubund einer 2%igen wäßrigen Emulsion von Phthalsäurediäthylester, Phthalsäurediallylester, Phthalsäuredihexylester, Kaliumsalz der 2-Methyl-3-zyklohexenkarbonsäure, Ammoniumsalz der 2-Methyl-3-zyklohexenkarbonsäure mit Hilfe einer Rückenspritze. Die Emulsion enthält 0,01 Masse% Tetrahydrofuran und 0,1 Masse% C12 -C14 -Kalziumalkylbenzolsulfonat.Plants of the winter wheat variety Polesskaya-70 are treated in the 5th period of organogenesis by atomizing and a 2% aqueous emulsion of diethyl phthalate, diallyphthalate phthalate, diphthalate phthalate, potassium salt of 2-methyl-3-cyclohexene carboxylic acid, ammonium salt of 2-methyl-3-carboxylic acid with the help of a backpack sprayer. The emulsion contains 0.01% by mass of tetrahydrofuran and 0.1% by mass of C 12 -C 14 calcium alkylbenzenesulfonate.

Der Verbrauch an Präparat beträgt 16 kg/ha. Als Kontrolle dienen Pflanzen, behandelt mit dem Verdünner ohne Sterilisationsmittel.The consumption of preparation is 16 kg / ha. Plants are used as a control, treated with the thinner without sterilizing agents.

Die Prüfergebnisse sind in der Tabelle 2 angegeben. Die ähnlichen Ergebnisse sind bei der Behandlung des Winterweizens Sorte Polesskaya-70 in der VI. Periode der Organogenese erhalten.

Figure imgb0004
The test results are shown in Table 2. The similar results are in the treatment of the winter wheat variety Polesskaya-70 in the VI. Preserved period of organogenesis.
Figure imgb0004

Beispiel 14-17Example 14-17

Pflanzen des Winterweizens Sorte Priboi werden in der V. und VI. Periode der Organogenese (nach Kupermann) mit einer 2%igen wäßrigen Emulsion von Kaliumsalz der 2-Methyl--3-zyklohexenkarbonsäure, 2-Methyl-3-zyklohexenkarbonsäure- methylester, Pnthalsäuredipropylester, Phthalsäurediisobutylester behandelt. Die Emulsion enthält 0,01 Masse% Dimethylsulfoxid und 0,1 Masse% C12-C14 -Kalziumalkylbenzolsulfonat. Der Verbrauch an Präparat beträgt 12 kg/ha. Als Kontrolle dienen Pflanzen, behandelt mit einem Verdünner ohne Sterilisationsmittel.Plants of the winter wheat variety Priboi are in the V. and VI. Period of organogenesis (according to Kupermann) treated with a 2% aqueous emulsion of potassium salt of 2-methyl-3-cyclohexenecarboxylic acid, 2-methyl-3-cyclohexenecarboxylic acid methyl ester, phthalic acid dipropyl ester, phthalic acid diisobutyl ester. The emulsion contains 0.01% by weight of dimethyl sulfoxide and 0.1% by weight of C 12 -C 14 calcium alkylbenzenesulfonate. The consumption of the preparation is 12 kg / ha. As Control is served by plants treated with a thinner without sterilizing agents.

Die Prüfergebnisse sind in der Tabelle 3 angegeben.

Figure imgb0005
The test results are shown in Table 3.
Figure imgb0005

Beispiele 18-22Examples 18-22

Pflanzen des Winterweizens Sorte Kharkovskaya 81 werden in der V. und VI. Periode der Organogenese (nach Kupermann) mit einer 2%igen wäßrigen Emulsion von Natriumsalz der 2-Methyl-3-zyklohexenkarbonsäure, Phthalsäuredihexylester, Ammoniumsalz der 2-Methyl-3-zyklohexenkarbon- säure, Phthalsäuredibutylester, Phthalsäurediallylester behandelt. Die Emulsion enthält 0,01 Masse% Dodezylsulfat und 0,1 Masse% C12-C14 -Kalziumalkylbenzolsulfonat. Der Verbrauch an Präparat beträgt 12 kg/ha.Plants of winter wheat variety Kharkovskaya 81 are in the V. and VI. Period of organogenesis (according to Kupermann) treated with a 2% aqueous emulsion of sodium salt of 2-methyl-3-cyclohexenecarboxylic acid, phthalic acid dihexyl ester, ammonium salt of 2-methyl-3-cyclohexenocarboxylic acid, phthalic acid dibutyl ester, phthalic acid diallyl ester. The emulsion contains 0.01% by mass of dodezyl sulfate and 0.1% by mass of C 12 -C 14 calcium alkylbenzenesulfonate. The consumption of the preparation is 12 kg / ha.

Die Prüfergebnisse sind in der Tabelle 4 angeführt. Als Kontrolle dienten Pflanzen, behandelt ähnlich wie in Beispiel 1.The test results are shown in Table 4. Plants served as controls, treated similarly to Example 1.

Figure imgb0006
Figure imgb0006

Beispiele 23 - 29Examples 23-29

Pflanzen des Sommerweizens Sorte Moskovskaya 35 werden in der V. Periode der Organogenese (nach Kupermann) mit einer 1%igen wäßrigen Emulsion von Kaliumsalz der 2-Methyl-3-zyklohexenkarbonsäure,2-Methyl-3-zyklohexenkarbon- äthylester, Phthalsäuredipropylester, Phthalsäurediallylester, Phthalsäurediisobutylester, Kaliumsalz der Benzoesäure behandelt. Die Emulsion enthält 0,01 Masse% Dimethylsulfoxid und 0,1 Masse% C12-C14-Kalziumalkylbenzolsulfonat. Der Verbrauch an Präparat beträgt 10 kg/ha. Als Kontrolle dienen Pflanzen, behandelt mit einem Verdünner ohne Sterilisationsmittel.Plants of the summer wheat variety Moskovskaya 35 are grown in the 5th period of organogenesis (according to Kupermann) with a 1% aqueous emulsion of potassium salt of 2-methyl-3-cyclohexene carboxylic acid, 2-methyl-3-cyclohexene carbonate, ethyl ester, phthalic acid dipropylester, phthalic acid dialyl ester, Diisobutyl phthalate, potassium salt of benzoic acid treated. The emulsion contains 0.01% by weight of dimethyl sulfoxide and 0.1% by weight of C 12 -C 14 calcium alkylbenzenesulfonate. The consumption of preparation is 10 kg / ha. Plants are used as a control, treated with a thinner without sterilizing agents.

Die PrÜfergebnisse sind in der Tabelle 5 angeführt. Die ähnlichen Ergebnisse sind bei der Behandlung des Sommerweizens Sorte Moskovskaya 35 in der VI. Periode der Organogenese erhalten.

Figure imgb0007
Figure imgb0008
 The test results are shown in Table 5. The similar results are in the treatment of the summer wheat variety Moskovskaya 35 in the VI. Preserved period of organogenesis.
Figure imgb0007
Figure imgb0008

Beispiele 30-33Examples 30-33

Pflanzen des Sommerweizens Sorte Botanicheskaya 4 werden in der V. Periode der Organogenese (nach kupermann) mit einer l%igen wäßrigen Emulsion von Phthalsäuredibutylester, Phthalsauredipropylester, Natriumsalz der 2-Methyl-3-zyklo- hexenkarbonsäure, 2-Methyl-3-zyklohexenkarbonsäuremethyl- ester behandelt. Die Emulsion enthalt 0,01 Masse% Tetrahydrofuran und 0,1 Masse% C12-C14-Kalziumalkylbenzolsulfonat. Der Verbrauch an Präparat beträgt 8 kg/ha. Als Kontrolle dienen Pflanzen, behandelt mit einem Verdünner ohne SterilisationsmittelPlants of the summer wheat variety Botanicheskaya 4 are in the 5th period of organogenesis (according to kupermann) with a 1% aqueous emulsion of dibutyl phthalate, diphtyl phthalate, sodium salt of 2-methyl-3-cyclohexenecarboxylic acid, 2-methyl-3-cyclohexenecarboxylic acid methyl- ester treated. The emulsion contains 0.01% by mass of tetrahydrofuran and 0.1% by mass of C 12 -C 14 calcium alkylbenzenesulfonate. The consumption of preparation is 8 kg / ha. Plants are used as a control, treated with a thinner without sterilizing agents

Die Prüfergebnisse sind in der Tabelle 6 angeführt. Die ähnlichen Ergebnisse sind bei der Behandlung des Sommerweizens Sorte Botanicheskaya 4 in der VI.Periode der Organogenese erhalten.

Figure imgb0009
The test results are shown in Table 6. The similar results are obtained in the treatment of the summer wheat variety Botanicheskaya 4 in the VIth period of organogenesis.
Figure imgb0009

Beispiele 34-36Examples 34-36

Pflanzen des Sommerweizens Sorte Rodina werden in der V. und VI. Periode der Organogenese (nach Kupermann) mit einer l%igen wäßrigen Emulsion von Ammoniumsalz der 2-Methyl-3-zyklohexenkarbonsäure, Phthalsäuredihexylester, Phthalsäurediisobutylester behandelt. Die Emulsion enthält 0,01 Masse% Dodezysulfat und 0,1 Masse% C12-C14--Kalziumalkylbenzolsulfonat. Der Verbrauch an Präparat beträgt 6 kg/ha. Als Kontrolle dienen Pflanzen, behandelt mit einem Verdünner ohne Sterilisationsmittel.Plants of the summer wheat variety Rodina are in the V. and VI. Period of organogenesis (according to Kupermann) with a 1% aqueous emulsion of ammonium salt of the 2-Me treated with ethyl 3-cyclohexene carboxylic acid, phthalic acid dihexyl ester, phthalic acid diisobutyl ester. The emulsion contains 0.01% by mass of dodezysulfate and 0.1% by mass of C 12 -C 14 - calcium alkylbenzenesulfonate. The consumption of the preparation is 6 kg / ha. Plants are used as a control, treated with a thinner without sterilizing agents.

Die Prüfergebnisse sind in der Tabelle 7 angeführt.

Figure imgb0010
The test results are shown in Table 7.
Figure imgb0010

Beispiele 37-42Examples 37-42

Pflanzen Tritikale der Sorte PRAG-109 werden in der V. Periode der Organogenese (nach Kupermann) mit einer 1%igen wäßrigen Emulsion von Phthalsäuredibutylester, Phthalsäurediäthylester, Phthalsäuredihexylester, Phthalsäurediisobutylester, Kaliumsalz der 2-Methyl-3-zyklohexenkarbon- säure, 2-Methyl-3-zyklohexenkarbonsäuremethylester behandelt. Die Emulsion enthält 0,01 Masse% Dimethylsulfoxid und 0,1 Masse% C12C14- Kalziumalkylbenzolsulfonat. Der Verbrauch an Präparat beträgt 10 kg/ha. Als Kontrolle dienen Pflanzen, behandelt mit einem Verdünner ohne Sterilisationsmittel.Plants Triticals of the PRAG-109 variety are used in the 5th period of organogenesis (according to Kupermann) with a 1% aqueous emulsion of dibutyl phthalate, diethyl phthalate, diphthalate phthalate, diisobutyl phthalate, potassium salt of 2-methyl-3-cyclohexarbonate -3-Cyclohexenkarbonsäuremethylester treated. The emulsion contains 0.01% by weight of dimethyl sulfoxide and 0.1% by weight of C 12 C 14 calcium alkylbenzenesulfonate. The consumption of preparation is 10 kg / ha. Plants are used as a control, treated with a thinner without sterilizing agents.

Die Prüfergebnisse sind in der Tabelle 8 angegeben. Die ähnlichen Ergebnisse sind bei der Behandlung von Tritikale der Sorte PRAG-109 in der VI. Periode der Organogenese erhalten.The test results are shown in Table 8. The similar results are for the treatment of triticals of the PRAG-109 variety in the VI. Preserved period of organogenesis.

Figure imgb0011
Figure imgb0011

Beispiele 43-4?Examples 43-4?

Pflanzen Tritikale Sorte Amfidiploid 206 werden in der V.Periode der Organogenese (nach Kupermann) mit einer l%igen wäßrigen Emulsion von Phthalsäuredipropylester, Phthalsäurediisobutylester, Kaliumsalz der 2-Methyl-3-zyklohexenkarbon- säure, 2-Methyl-3-zyklohexenkarbonsäuremethylester, Ammoniumsalz der 2-Methyl-3-zyklohexenkarbonsäure behandelt. Die Emulsion enthält 0,01 Masse% Tetrahydrofuran und 0,1 Masse% C12-C14-Kalziumalkylbenzolsulfonat. Der Verbrauch an Präparat beträgt 6 kg/ha. Als Kontrolle dienen Pflanzen, behandelt mit einem Verdünner ohne Sterilisationsmittel.Plants Trical type Amfidiploid 206 are in the 5th period of organogenesis (according to Kupermann) with a 1% aqueous emulsion of phthalic acid dipropyl ester, phthalic acid diisobutyl ester, potassium salt of 2-methyl-3-cyclohexenecarboxylic acid, 2-methyl-3-cyclohexyl carbonic acid, ammonium carbonic acid the 2-methyl-3-cyclohexene carboxylic acid treated. The emulsion contains 0.01% by mass of tetrahydrofuran and 0.1% by mass of C 12 -C 14 calcium alkylbenzenesulfonate. The consumption of the preparation is 6 kg / ha. Plants are used as a control, treated with a thinner without sterilizing agents.

Die Prüfergebnisse sind in der Tabelle 9 angegeben. Die ähnlichen Ergebnisse sind bei der Behandlung von Tririkale Sorte Amfiploid 206 in der VI. Periode der Organogenese erhalten.

Figure imgb0012
The test results are shown in Table 9. The similar results are in the treatment of trirical variety Amfiploid 206 in the VI. Preserved period of organogenesis.
Figure imgb0012

Beispiele 48-55Examples 48-55

Pflanzen von tetraploidem Roggen Sorte Belta werden in der V. Periode der Organogenese (nach Kupermann) mit einer 1%igen wäßrigen Emulsion von Kaliumsalz der 2-Methyl-3-zy- klohexenkarbonsäure, 2-Methyl-3-zyklohexenkarbonsäuremethyl- ester, Phthalsäuredibutylester, Phthalsäuredihexylester, Phthalsäuredipropylester, Phthalsäurediallylester, Phthalsäurediisobutylester, Kaliumsalz der p-Hydroxysäure behandelt. Die Emulsion enthält 0,01 Masse% Dimethylsuloxid und 0,1 Masse% C12-C14-Kalziumalkylbenzolsulfonat. Der Verbrauch an Präparat beträgt 6 kg/ha. Als Kontrolle dienen Pflanzen behandelt mit einem Verdünner ohne Sterilisationsmittel.Plants of tetraploid rye variety Belta are in the 5th period of organogenesis (according to Kupermann) with a 1% aqueous emulsion of potassium salt of 2-methyl-3-cyclohexene carboxylic acid, 2-methyl-3-cyclohexene carboxylic acid methyl ester, phthalic acid dibutyl ester, Treated phthalic acid dihexyl ester, phthalic acid dipropyl ester, phthalic acid diallyl ester, phthalic acid diisobutyl ester, potassium salt of p-hydroxy acid. The emulsion contains 0.01% by weight of dimethyl suloxide and 0.1% by weight of C 12 -C 14 calcium alkylbenzenesulfonate. The consumption of the preparation is 6 kg / ha. Plants treated with a thinner without sterilizing agents serve as a control.

Die Prüfergebnisse sind in der Tabelle 10 angegeben. Die ännlichen Ergebnisse sind bei der Behandlung von tetraploidem Roggen Sorte Belta in der VI. Periode der Organogenese erhalten.

Figure imgb0013
The test results are shown in Table 10. The similar results are in the treatment of tetraploid rye variety Belta in the VI. Preserved period of organogenesis.
Figure imgb0013

Beispiele 56-59Examples 56-59

Pflanzen von tetraploidem Roggen Sorte Ukrainskaya werden in der V. Periode der Organogenese (nach Kupermann) mit einer wäßrigen Emulsion von Ammoniumsalz der 2-Methyl-3--zyklohexenkarbonsäure, Phthalsäurediäthylester, Kaliumsalz der Benzoesäure, Phthalsäurediisobutylester behandelt. Die Emulsion enthält 0,01 Masse% Dimethylformamid und 0,1 Masse% C12-C14-Kalziumalkylbenzolsulfonat. Der Verbrauch an Präparat beträgt 6 kg/ha. Als Kontrolle dienen Pflanzen, behandelt mit einem Verdünner ohne Sterilisationsmittel. Die Prüfergebnisse sind in der Tabelle 11 angeführt. Die ähnlichen Ergebnisse sind bei der Behandlung von tetraploidem Roggen Sorte Ukrainskaya in der VI. Periode der Organogenese erhalten.

Figure imgb0014
Plants of tetraploidal rye of the Ukrainskaya variety are treated in the 5th period of organogenesis (according to Kupermann) with an aqueous emulsion of ammonium salt of 2-methyl-3-cyclohexenecarboxylic acid, diethyl phthalate, potassium salt of benzoic acid, diisocyanate phthalate. The emulsion contains 0.01 mass% dimethylformamide and 0.1 mas se% C12-C14 calcium alkylbenzenesulfonate. The consumption of the preparation is 6 kg / ha. Plants are used as a control, treated with a thinner without sterilizing agents. The test results are shown in Table 11. The similar results are in the treatment of tetraploid rye variety Ukrainskaya in the VI. Preserved period of organogenesis.
Figure imgb0014

Beispiele 60-67Examples 60-67

Pflanzen von diploidem Roggen Sorte Chulpan werden in der V. Periode der Organogenese (nach Kupermann) mit einer 1%igen wäßrigen Emulsion von Kaliumsalz der 2-Methyl-3-zy- klohexenkarbonsäure, 2-Methyl-3-zyklohexenkarbonsäuremethyl- ester, Kaliumsalz der Salizylsäure, Phthalsäurediallylester, Phthalsäurediisobutylester, Phthalsäuredipropylester, Phthalsäuredihexylester, Phthalsäuredibutylester. Die Emulsion enthält 0,01 Masse% Tetrahydrofuran und 0,1 Masse% C12-C14--Kalziumalkylbenzolsulfonat. Der Verbrauch an Präparat beträgt 8 kg/ha. Als Kuntrolle dienen Pflanzen, behandelt mit einem Verdünner ohne Sterilisationsmittel.Plants of diploid rye Chulpan are grown in the 5th period of organogenesis (according to Kupermann) with a 1% aqueous emulsion of potassium salt of 2-methyl-3-cyclohexene carboxylic acid, 2-methyl-3-cyclohexene carboxylic acid methyl ester, potassium salt of Salicylic acid, phthalic acid diallyl ester, phthalic acid diisobutyl ester, phthalic acid dipropyl ester, phthalic acid dihexyl ester, phthalic acid dibutyl ester. The emulsion contains 0.01% by mass of tetrahydrofuran and 0.1% by mass of C12-C14 - calcium alkylbenzenesulfonate. The consumption of preparation is 8 kg / ha. Plants, treated with a thinner without sterilizing agents, serve as an art roll.

Die Prüfergebnisse sind in der Tabelle 12 angeführt. Die ähnlichen Ergebnisse sind bei der Behandlung von diploidem Roggen Sorte Chulpan in der VI. Periode der Organogenese erhalten.The test results are shown in Table 12. The similar results are in the treatment of diploid rye Chulpan in the VI. Preserved period of organogenesis.

Figure imgb0015
Figure imgb0015

Beispiele 68-73Examples 68-73

Pflanzen von diploidem Roggen Sorte Kharkovskaya 55 werden in der V. und VI. Periode der Organogenese (nach Kupermann) mit einer 1%igen wäßrigen Emulsion von Phthalsäuredibutylester, Phthalsäurediisobutylester, Phthalsäurediallylester, Phthalsäuredihexylester, 2-Methyl-3-zyklohexen- karbonsäuremethylester, Natriumsalz der 2-Methyl-3-zyklohex- enkarbonsäure behandelt. Die Emulsion enthält 0,01 Masse% Dimethylformamid und 0,1 Masse% C12C14-Kalziumalkylbenzolsulfonat.Plants of diploid rye variety Kharkovskaya 55 are in the V. and VI. Period of organogenesis (according to Kupermann) with a 1% aqueous emulsion of phthalic acid dibutyl ester, phthalic acid diisobutyl ester, phthalic acid diallyl ester, phthalic acid dihexyl ester, 2-methyl-3-cyclohexene-carboxylic acid methyl ester, sodium salt of 2-methyl-3-cyclohexanoic acid. The emulsion contains 0.01% by weight of dimethylformamide and 0.1% by weight of C 12 C 14 calcium alkylbenzenesulfonate.

Der Verbrauch an Präparat beträgt 6 kp/ha. Als Kontrolle dienen Pflanzen, benandelt mit einem Verdünner ohne Sterilisationsmittel.The consumption of preparation is 6 kp / ha. Plants, treated with a thinner without sterilizing agent, serve as a control.

Die Prüfergebnisse sind in der Tabelle 13 angeführt.

Figure imgb0016
The test results are shown in Table 13.
Figure imgb0016

Beispiele 74-75Examples 74-75

Pflanzen von diploidem Roggen Sorte Belorusskaya 23 werden in der V. und VI. Periode der Organogenese (nach Kupermann) mit einer 1%igen wäßrigen Emulsion von Phthalsäuredibutylester, Kaliumsalz der 2-Methyl-3-zyklohexenkarbonsäure behandelt. Die Emulsion enthält 0,01 Masse% Dodezylsulfat, und 0,1 Masse% C12-C14-Kalziumalkylbenzolsulfonat.Plants of diploid rye variety Belorusskaya 23 are in the V. and VI. Period of organogenesis (according to Kupermann) treated with a 1% aqueous emulsion of phthalic acid dibutyl ester, potassium salt of 2-methyl-3-cyclohexene carboxylic acid. The emulsion contains 0.01% by mass of dodezyl sulfate and 0.1% by mass of C 12 -C 14 calcium alkylbenzenesulfonate.

Der Verbrauch an Präparat beträgt 6 kg/ha. Als Kontrolle dienen Pflanzen, behandelt mit einem Verdünner ohne Sterilisationsmittel.The consumption of the preparation is 6 kg / ha. Plants are used as a control, treated with a thinner without sterilizing agents.

Die Prüfergebnisse sind in der Tabelle 14 angeführt.

Figure imgb0017
The test results are shown in Table 14.
Figure imgb0017

Beispiele 76-81Examples 76-81

Pflanzen von diploidem Roggen Sorte Voskhod 2 werden in der V. Periode der Organogenese (nach Kupermann) mit einer l%igen wäßrigen Emulsion von Phthalsäurediäthylester, Phthalsaurediisobutylester, Kaliumsalz der 2-Methyl-3-zyklohexen- karbonsäure, Ammoniumsalz der 2-Methyl-3-zyklohexenkarbon- säure, 2-Methyl-3-zyklohexenkarbonsäuremethylester, Phthalsaurediallylester behandelt.Plants of diploid rye variety Voskhod 2 are in the 5th period of organogenesis (according to Kupermann) with a 1% aqueous emulsion of phthalate, phthal acid diisobutyl ester, potassium salt of 2-methyl-3-cyclohexenecarboxylic acid, ammonium salt of 2-methyl-3-cyclohexenecarboxylic acid, methyl 2-methyl-3-cyclohexenecarboxylate, phthalic acid diallyl ester.

Die Emulsion enthält 0,01 Masse% Dodezylsulfat und 0,1 Masse% C12-C14-Kalziumalkylbenzolsulfonat. Der Verbrauch an Präparat beträgt 10 kg/ha, Als Kontrolle dienen Pflanzen, behandelt mit einem Verdünner ohne Sterilisationsmittel.The emulsion contains 0.01% by mass of dodezyl sulfate and 0.1% by mass of C 12 -C 14 calcium alkylbenzenesulfonate. The consumption of preparation is 10 kg / ha, plants are used as a control, treated with a thinner without sterilizing agent.

Die Prufergebnisse sind in der Tabelle 15 angeführt. Die ählichen Ergebnisse sind bei der Behandlung von diploidem Roggen Sorte Voskhod 2 in der VI. Periode der Organogenese erhalten.

Figure imgb0018
The test results are shown in Table 15. The similar results are in the treatment of diploid rye Voskhod 2 in the VI. Preserved period of organogenesis.
Figure imgb0018

Beispiele 82-88Examples 82-88

Pflanzen von diploidem Roggen Sorte Gibrid 1861/79 werden in der V. Periode der Organogenese (nach Kupermann) mit einer 1%igen wäßrigen Emulsion von Phthalsäurediisobutylester, Kaliumsalz der 2-Methyl-3-zyklohexenkarbonsäure, 2--Methyl-3-zyklohexenkarbonsäuremethylester, Ammoniumsalz der 2-Methyl-3-zyklohexenkarbonsäure, Phthalsäurediallylester, Phthalsäuredihexylester, Ammoniumsalz der p-Hydroxybenzoesäure behandelt. Die Emulsion enthält 0,01 Masse% Dimethylsulfoxid und 0,1 Masse% C12-C14-Kalziumalkylbenzolsulfonat. Der Verbrauch an Präparat beträgt 6 kg/ha. Als Kontrolle dienen Pflanzen, behandelt mit einem Verdünner ohne Sterilisationsmittel.Plants of diploid rye variety Gibrid 1861/79 are in the 5th period of organogenesis (according to Kupermann) with a 1% aqueous emulsion of di-phthalic acid isobutyl ester, potassium salt of 2-methyl-3-cyclohexene carboxylic acid, 2-methyl-3-cyclohexene carboxylic acid methyl ester, Treated ammonium salt of 2-methyl-3-cyclohexenecarboxylic acid, diallyl phthalate, di-phthalate, ammonium salt of p-hydroxybenzoic acid. The emulsion contains 0.01% by weight of dimethyl sulfoxide and 0.1% by weight of C 12 -C 14 calcium alkylbenzenesulfonate. The consumption of the preparation is 6 kg / ha. Plants treated with a thinner without are used as a control Sterilizing agents.

Die Prüfergebnisse sind in der Tabelle 16 angeführt. Die ähnlichen Ergebnisse sind bei der Behandlung von diploidem Roggen Sorte Gibrid 1861/79 in der VI. Periode der Organogenese erhalten.

Figure imgb0019
The test results are shown in Table 16. The similar results are in the treatment of diploid rye variety Gibrid 1861/79 in the VI. Preserved period of organogenesis.
Figure imgb0019

Beispiele 89-96Examples 89-96

Pflanzen der Hirse Sorte Mironovskoe 94 werden in der V. Periode der Organogenese (nach Kupermann) mit einer l%igen wäßrigen Emulsion von Kaliumsalz der 2-Methyl-3-zyklohexen- karbonsäure, 2-Methyl-3-zyklohexenkarbonsäuremethylester, Phthalsäuredihexylester, Phthalsäuredibutylester, Phthalsäuredipropylester, Natriumsalz der p-Hydroxybenzoesäure, Phthalsäurediäthylester, Phthalsäurediallylester behandelt. Die Emulsion enthält 0,01 Masse% Dimethylformamid und 0,1 Masse% C12-C14-Kalziumalkylbenzolsulfonat. Der Verbrauch an Präparat beträgt 10 kg/ha. Als Kontrolle dienen Pflanzen, behandelt mit einem Verdünner ohne Sterilisationsmittel. Die Prüfergebnisse sind in der Tabelle 17 angeführt. Die ähnlichen Ergebnisse sind bei der Behandlung der Hirse Sorte Mironovskoe 94 in der VI. Periode der Organogenese erhalten.

Figure imgb0020
Plants of the millet variety Mironovskoe 94 are in the 5th period of organogenesis (according to Kupermann) with a 1% aqueous emulsion of potassium salt of 2-methyl-3-cyclohexenecarboxylic acid, 2-methyl-3-cyclohexenecarboxylic acid methyl ester, phthalic acid dihexyl ester, phthalic acid dibutyl ester, Treated phthalic acid dipropylester, sodium salt of p-hydroxybenzoic acid, diethyl phthalate, diallyl phthalate. The emulsion contains 0.01% by weight of dimethylformamide and 0.1% by weight of C 12 -C 14 calcium alkylbenzenesulfonate. The consumption of preparation is 10 kg / ha. Plants are used as a control, treated with a thinner without sterilizing agents. The test results are shown in Table 17. The similar results are for the treatment of millet variety Mironovskoe 94 in the VI. Preserved period of organogenesis.
Figure imgb0020

Beispiele 97-102Examples 97-102

Pflanzen der Hirse Sorte K-9693 Kormovoe I werden in der V. Periode der Organogenese (nach Kupermann) mit einer 1%igen wäßrigen Emulsion von Ammoniumsalz der 2-Methyl-3-zyklo- nexenkarbonsäure, Phthalsäuredipropylester, Phthalsäuredibutylester, Phthalsäurediisobutylester, 2-Methyl-3-zyklo- hexenkarbonsäuremethylester, Phthalsäuredihexylester behandelt. Die Emulsion enthält 0,01 Masse% Dodezylsulfat und 0,1 Masse% C12-C14-Kalziumalkylbenzolsulfonat. Der Verbrauch an Präparat beträgt 8 kg/ha. Als Kontrolle dienen Pflanzen, behandelt mit einem Verdünner ohne Sterilisationsmittel. Die Prüfergebnisse sind in der Tabelle 18 angeführt. Die ähnlichen Ergebnisse sind bei der Behandlung der Hirse Sorte K-9693 Kormovoe I in der VI. Periode der Organogenese erhalten.

Figure imgb0021
Plants of the millet variety K-9693 Kormovoe I are in the 5th period of organogenesis (according to Kupermann) with a 1% aqueous emulsion of ammonium salt of 2-methyl-3-cyclonexenecarboxylic acid, phthalic acid dipropyl ester, phthalic acid dibutyl ester, phthalic acid diisobutyl ester, 2-methyl -3-Cyclohexenkarbonsäuremethylester, phthalic acid dihexyl treated. The emulsion contains 0.01% by mass of dodezyl sulfate and 0.1% by mass of C 12 -C 14 calcium alkylbenzenesulfonate. The consumption of preparation is 8 kg / ha. Plants are used as a control, treated with a thinner without sterilizing agents. The test results are shown in Table 18. The similar results are in the treatment of millet variety K-9693 Kormovoe I in VI. Preserved period of organogenesis.
Figure imgb0021

Baispiele 103-116Examples 103-116

Pflanzen der Sonnenblume Sorte Peredovik werden in der V. Periode der Organogenese (nach Kupermann) mit einer 0,5%igen wäßrigen Emulsion von Phthalsäuredibutylester, Phthalsäurediäthylester, Kaliumsalz der 2-Methyl-3-zyklohexenkarbonsäu- re, Natriumsalz der 2-Methyl-3-zyklohexenkarbonsäure sowie mit einer 0,05%igen wäßrigen Emulsion von 2-Methyl-3-zyklo- hexenkarbonsäuremethylester behandelt. Die Emulsion enthält 0,01 Masse% Dimethylsulfoxid und 0,1 Masse% C12-C14-Kalziumalkylbenzolsulfonat. Die Sonnenblume Linie VK-119 werden mit einer 0,2%igen wäßrigen Emulsion von Phthalsäuredibutylester, 0,1%igen wäßrigen Emulsion von Phthalsäurediäthylester, Kaliumsalz der 2-Methyl-3-zyklohexenkarbonsäure, 1%igen wäßrigen Emulsion von Natriumsalz der. 2-Methyl-3-zyklohexen- karbonsäure und 0,01%igen wäßrigen Emulsion von 2-Methyl--3-zyklohexenkarbonsäuremethylester behandelt. Die Emulsion enthält 0,01 Masse% Dimethylformamid und 0,1 Masse% C12-C14--Kalziumalkylbenzolsulfonat.Plants of the Peredovik sunflower variety are grown in the 5th period of organogenesis (according to Kupermann) with a 0.5% aqueous emulsion of dibutyl phthalate, diethyl phthalate, potassium salt of 2-methyl-3-cyclohexene carboxylic acid, sodium salt of 2-methyl-3 cyclohexene carboxylic acid and treated with a 0.05% aqueous emulsion of 2-methyl-3-cyclohexene carboxylic acid methyl ester. The emulsion contains 0.01% by weight of dimethyl sulfoxide and 0.1% by weight of C 12 -C 14 calcium alkylbenzenesulfonate. The sunflower line VK-119 are with a 0.2% aqueous emulsion of phthalic acid dibutyl ester, 0.1% aqueous emulsion of phthalic acid diethyl ester, potassium salt of 2-methyl-3-cyclohexenecarboxylic acid, 1% aqueous emulsion of sodium salt. Treated 2-methyl-3-cyclohexenecarboxylic acid and 0.01% aqueous emulsion of 2-methyl - 3-cyclohexenecarboxylic acid methyl ester. The emulsion contains 0.01% by weight of dimethylformamide and 0.1% by weight of C 12 -C 14 calcium alkylbenzenesulfonate.

Die Sonnenblume Linie BK-373 werden mit einer 0,2%igen wäßrigen Emulsion von Phthalsäuredibutylester, 0,1%igen wäßrigen Emulsion von Kaliumsalz der 2-Methyl-3-zyklohexylkar- bonsäuremethylester und 0,2%igen wäßrigen Emulsion von Phthalsäurediäthylester behandelt. Die Emulsion enthält 0,01 Masse% Dodezylsulfat und 0,1 Masse% C12-C14-Kalziumalkylbenzolsulfonat.The sunflower line BK-373 are treated with a 0.2% aqueous emulsion of phthalic acid dibutyl ester, 0.1% aqueous emulsion of potassium salt of the 2-methyl-3-cyclohexylcarboxylic acid methyl ester and 0.2% aqueous emulsion of phthalic acid diethyl ester. The emulsion contains 0.01 % By mass of dodezyl sulfate and 0.1% by weight of C12-C14 calcium alkylbenzenesulfonate.

Als Kontrolle in allen Fällen dienen Pflanzen, behandelt mit einem Verdünner ohne Sterilisationsmittel.Plants, treated with a thinner without sterilizing agent, serve as a control in all cases.

Die Prüfergebnisse sind in der Tabelle 19 angeführt. Die ähnlichen Ergebnisse sind bei der Behandlung der Sonnenblume der genannten Sorten in der VI. Periode der Organogenese erhalten.

Figure imgb0022
Figure imgb0023
 The test results are shown in Table 19. The similar results are in the treatment of the sunflower of the varieties mentioned in the VI. Preserved period of organogenesis.
Figure imgb0022
Figure imgb0023

Beispiel 117-126Example 117-126

Pflanzen des Winterweizens Sorte Mironovskaya 808 werden in der V. Periode der Organogenese (nach Kupermann) mit einer 2%igen wäßrigen Emulsion eines Gemisches aus Phthalsäurediäthylester mit Kaliumsalz der Salizylsäure (Verhältnis 1:1), mit einer 2%igen wäßrigen Emulsion eines Gemisches aus Phthalsäuredipropylester mit Kaliumsalz der Benzoesäure (Verhältnis 1:1), mit einer 2%igen wäßrigen Emulsion eines Gemisches aus Phthalsäuredibutylester und Kaliumsalz von p-Hydroxybenzoesäure (Verhaltnis 1:1) behandelt.Plants of the winter wheat variety Mironovskaya 808 are made in the 5th period of organogenesis (according to Kupermann) with a 2% aqueous emulsion of a mixture of diethyl phthalate with potassium salt of salicylic acid (ratio 1: 1), with a 2% aqueous emulsion of a mixture Phthalic acid dipropyl ester with potassium salt of benzoic acid (ratio 1: 1), treated with a 2% aqueous emulsion of a mixture of phthalic acid dibutyl ester and potassium salt of p-hydroxybenzoic acid (ratio 1: 1).

Die Emulsion enthält 0,01 Masse% Tetrahydrofuran und 0,1 Masse% C12-C14-Kalziumalkylbenzolsulfonat. Der Verbrauch an Präparat beträgt 12 kg/ha.The emulsion contains 0.01% by mass of tetrahydrofuran and 0.1% by mass of C12-C14 calcium alkylbenzenesulfonate. The consumption of the preparation is 12 kg / ha.

Pflanzen des Sommerweizens Moskovskaya werden mit einer 1,0%igen wäßrigen Emulsion eines Gemisches aus Phthalsäurediisobutylester mit Kaliumsalz der Benzoesäure (Verhältnis 1:1), mit einer 1,0%igen wäßrigen Emulsion eines Gemisches aus Phthalsäuredihexylester mit Kaliumsalz der p-Hydroxybenzoesäure (Verhältnis 1:1), mit einer 1,0%igen wäßrigen Emulsion eines Gemisches aus Phthalsäurediallylester mit Kaliumsalz der Benzoesäure behandelt. Die Emulsion enthält 0,01 Masse% Dimethylsulfoxid und 0,1 Masse% C12-C14-Kalziumalkyl-benzolsulfonat. Der Verbrauch an Präparat beträgt 6 kg/ha.Plants of the Moskovskaya summer wheat are treated with a 1.0% aqueous emulsion of a mixture of diisocyanate phthalate with potassium salt of benzoic acid (ratio 1: 1), with a 1.0% aqueous emulsion of a mixture of diphthalate phthalate with potassium salt of p-hydroxybenzoic acid (ratio 1: 1), treated with a 1.0% aqueous emulsion of a mixture of diallyl phthalate with potassium salt of benzoic acid. The emulsion contains 0.01% by weight of dimethyl sulfoxide and 0.1% by weight of C 12 -C 14 calcium alk y l-benzenesulfonate. The consumption of the preparation is 6 kg / ha.

Pflanzen von diploidem Roggen Chulpan werden mit einer l%igen wäßrigen Emulsion eines Gemisches aus Phthalsäuredihexylester mit Kaliumsalz der p-Hydroxybenzoesäure, mit einer l%igen wäßrigen Emulsion eines Gemisches aus Phthalsäurediallylester mit Kaliumsalz der Salizylsäure (Verhältnis 1:1), mit einer 1%igen wäßrigen Emulsion eines Gemisches aus Phthalsäuredibutylester mit Kaliumsalz der Benzoesäure (Verhältnis 1:1), mit einer 1%igen wäßrigen Emulsion eines Gemisches aus Phthalsäurediisobutylester und Phthalsäurediäthylester (Verhältnis 1:1) behandelt. Die Emulsion enthält 0,01 Masse% Tetrahydrofuran und 0,1 Masse% C12-C14-Kalziumalkylbenzolsulfonat. Der Verbrauch an Präparat beträgt 6 kg/ha.Plants of diploid rye Chulpan are treated with a 1% aqueous emulsion of a mixture of phthalic acid dihexyl ester with potassium salt of p-hydroxybenzoic acid, with a 1% aqueous emulsion of a mixture of phthalic acid diallyl ester with potassium salt of salicylic acid (ratio nis 1: 1), treated with a 1% aqueous emulsion of a mixture of phthalic acid dibutyl ester with potassium salt of benzoic acid (ratio 1: 1), with a 1% aqueous emulsion of a mixture of phthalic acid diisobutyl ester and phthalic acid diethyl ester (ratio 1: 1). The emulsion contains 0.01% by mass of tetrahydrofuran and 0.1% by mass of C 12 -C 14 calcium alkylbenzenesulfonate. The consumption of the preparation is 6 kg / ha.

Pflanzen Tritikale Sorte PRAG-109 werden mit einer l%igen wäßrigen Emulsion eines Gemiscnes aus Phthalsäuredibutylester mit Kaliumsalz der Salizylsäure (Verhältnis 1:1), mit einer wäßrigen Emulsion eines Gemisches aus Phthalsäuredihexylester mit Kaliumsalz der Benzoesäure (Verhältnis 1:1), mit einer 1%igen wäßrigen Emulsion aus Phthalsäurediallylester mit Kaliumsalz der p-Hydroxybenzoesäure (Verhältnis 1:1) behandelt. Die Emulsion enthält 0,01 Masse% Terahydrofuran und 0,1 Masse% C12-C14-Kalziumalkylbenzolsulfonat. Der Verbrauch an Präparat beträgt 8 kg/ha.Plants Triticale variety PRAG-109 are mixed with a 1% aqueous emulsion of a mixture of phthalic acid dibutyl ester with potassium salt of salicylic acid (ratio 1: 1), with an aqueous emulsion of a mixture of phthalic acid dihexyl ester with potassium salt of benzoic acid (ratio 1: 1) 1% aqueous emulsion of phthalic acid diallyl ester treated with potassium salt of p-hydroxybenzoic acid (ratio 1: 1). The emulsion contains 0.01% by mass of terahydrofuran and 0.1% by mass of C 12 -C 14 calcium alkylbenzenesulfonate. The consumption of preparation is 8 kg / ha.

In allen Fällen dienen als Kontrolle Pflanzen, behandelt mit einem Verdünner ohne Sterilisationsmittel. Die Prüfergebnisse sind in der Tabelle 20 angeführt. Die ähnlichen Ergebnisse sind bei der Behandlung der genannten Pflanzen in der VI. Periode der Organogenese erhalten.

Figure imgb0024
Figure imgb0025
 In all cases, plants are used as a control, treated with a thinner without sterilizing agents. The test results are shown in Table 20. The similar results are in the treatment of the plants mentioned in VI. Preserved period of organogenesis.
Figure imgb0024
Figure imgb0025

Gewerbliche VerwertbarkeitCommercial usability

Das anmeldungsgemäße Verfahren findet Anwendung in der Selektion und im Samenbau zur Erzielung hochproduktiver Sorten von Hybriden und landwirtschaftlichen Kulturen.The method according to the application is used in selection and seed production to achieve highly productive varieties of hybrids and agricultural crops.

Claims (4)

1. Verfahren zur Sterilisation der Staubbeutel von Pflanzen durch ihre Behandlung mit einem Sterilisationsmittel in Verbindung mit einem Verdünner in der fünften und/oder sechsten Periode der Organogenese, dadurcn gekenn-zeichnet, daß als Sterilisationsmittel Karbonsäurederivate der allgemeinen Formel A-COOR, worin R für K, Na, NH4, Alkyl mit 1 bis 6 Kohlenstoffatomen Allyl steht.
Figure imgb0026
bedeutet, worin R 1 für COOH, COOR, H, OH steht, R2 für H, OH steht, oder deren Gemische verwendet werden.1. Process for the sterilization of the anthers of plants by their treatment with a sterilizing agent in conjunction with a thinner in the fifth and / or sixth period of organogenesis, characterized in that as the sterilizing agent carboxylic acid derivatives of the general formula A-COOR, wherein R for K, Na, NH 4 , alkyl having 1 to 6 carbon atoms allyl.
Figure imgb0026
 means where R 1 is COO H , COOR, H, OH, R 2 is H, OH, or mixtures thereof are used. 2. Verfahren nach Anspruch 1, dadurch gekenn-zeichnet, daß die genannten Karbonsäurederivate in Verbindung mit einem Verdünner in Form einer 0,01 - bis 2%igen wäßrigen Emulsion verwendet werden.2. The method according to claim 1, characterized in that said carboxylic acid derivatives are used in conjunction with a thinner in the form of a 0.01% to 2% aqueous emulsion. 3. Verfahren nach Anspruch 1-2, dadurch gekenn-zeichnet, daß als mit dem Sterilisationsmittel zu behandelnde Pflanzen Gräser und Sonnenblume dienen.3. The method according to claim 1-2, characterized in that grasses and sunflower serve as plants to be treated with the sterilizing agent. 4. Verfahren nach Anspruch 1 bis 3, dadurch gekenn- zeichnet, daß man zur Erzielung eines hohen Sterilisationsgrades von Staubbeuteln unter ungünstigen klimatischen Bedingungen eine wiederholte Behandlung von Pflanzen mit dem Sterilisationsmittel in der fünften und/oder sechsten Periode der Organogenese durchführt.4. The method according to claim 1 to 3, characterized in that to achieve a high degree of sterilization of dust bags under unfavorable climatic conditions, repeated treatment of plants with the sterilizing agent in the fifth and / or sixth period of organogenesis.
EP19880905465 1988-03-17 1988-03-17 Method of sterilizing plant pollen Withdrawn EP0364581A1 (en)

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WO1989008399A1 (en) * 1988-03-17 1989-09-21 Vsesojuzny Nauchno-Issledovatelsky Institut Selsko Method of sterilizing plant pollen
AU609211B2 (en) * 1988-03-17 1991-04-26 Institut Elementoorganicheskikh Soedineny Imeni A.N.Nesmeyanova Akademii Nauk Sssr Method of sterilizing plant anthers using polybrominated alkanes or chlorinated derivatives
JPH02503563A (en) * 1988-03-17 1990-10-25 フセソユズニ　ナウチノ‐イススレドバテルスキ　インスティテュト　セルスコホズヤイストベンノイ　ビオテフノロギイ　フセソユズノイ　アカデミイ　セルスコホズヤイストベンニフ　ナウク　イメニ　ベー．イー．レニナ Method for making anthers sterile

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SU931087A3 (en) * 1976-05-24 1982-05-23 Ром Энд Хаас Компани (Фирма) Method and composition for inducing male sterility in lucritive cereals
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US4459152A (en) * 1981-04-14 1984-07-10 Ciba-Geigy Corporation Nitroarylalkylsulfone derivatives as plant growth stimulants
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WO1989008399A1 (en) * 1988-03-17 1989-09-21 Vsesojuzny Nauchno-Issledovatelsky Institut Selsko Method of sterilizing plant pollen
AU609211B2 (en) * 1988-03-17 1991-04-26 Institut Elementoorganicheskikh Soedineny Imeni A.N.Nesmeyanova Akademii Nauk Sssr Method of sterilizing plant anthers using polybrominated alkanes or chlorinated derivatives

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